Streamlined structure elucidation of an unknown compound in a pigment formulation

Yüce, Imanuel; Morlock, Gertrud E.

doi:10.1016/j.chroma.2016.09.040

Cited by 20 publications

(4 citation statements)

References 36 publications

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“…Although higher sample volumes can be applied to a preparative TLC plate, the transition from analytical to preparative TLC plate is time consuming and costly. In addition, a reduction of the separation performance and resolution on higher‐thickness plates (0.5, 1, and 2 mm) was reported 36 . Therefore, using an analytical plate of 0.25 mm thickness, low amounts of bioactive bands (< 1 mg) were isolated and analysed by UHPLC‐MS.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, a reduction of the separation performance and resolution on higher-thickness plates (0.5, 1, and 2 mm) was reported. 36 Therefore, using an analytical plate of 0.25 mm thickness, low amounts of bioactive bands (< 1 mg) were isolated and analysed by UHPLC-MS. Then, bands with the same hR F and molecular mass were grouped resulting in nine different bands (Figure 1). Band 1 and 2 inhibited α-amylase and were only found in LF-1.…”

Section: Bioassay-guided Fractionation and Isolation: Tlc-bioautographymentioning

confidence: 99%

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Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Galarce‐Bustos,

Obregón,

Vallejos‐Almirall

et al. 2023

Phytochemical Analysis

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IntroductionType 2 diabetes mellitus is a globally prevalent chronic disease characterised by hyperglycaemia and oxidative stress. The search for new natural bioactive compounds that contribute to controlling this condition and the application of analytical methodologies that facilitate rapid detection and identification are important challenges for science. Annona cherimola Mill. is an important source of aporphine alkaloids with many bioactivities.ObjectiveThe aim of this study is to isolate and identify antidiabetic compounds from alkaloid extracts with α‐glucosidase and α‐amylase inhibitory activity from A. cherimola Mill. leaves using an effect‐directed analysis by thin‐layer chromatography (TLC)–bioautography.MethodologyGuided fractionation for α‐glucosidase and α‐amylase inhibitors in leaf extracts was done using TLC–bioassays. The micro‐preparative TLC was used to isolate the active compounds, and the identification was performed by mass spectrometry associated with web‐based molecular networks. Additionally, in vitro estimation of the inhibitory activity and antioxidant capacity was performed in the isolated compounds.ResultsFive alkaloids (liriodenine, dicentrinone, N‐methylnuciferine, anonaine, and moupinamide) and two non‐alkaloid compounds (3‐methoxybenzenepropanoic acid and methylferulate) with inhibitory activity were isolated and identified using a combination of simple methodologies. Anonaine, moupinamide, and methylferulate showed promising results with an outstanding inhibitory activity against both enzymes and antioxidant capacity that could contribute to controlling redox imbalance.ConclusionsThese high‐throughput methodologies enabled a rapid isolation and identification of seven compounds with potential antidiabetic activity. To our knowledge, the estimated inhibitory activity of dicentrinone, N‐methylnuciferine, and anonaine against α‐glucosidase and α‐amylase is reported here for the first time.

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Section: Resultsmentioning

confidence: 99%

Section: Bioassay-guided Fractionation and Isolation: Tlc-bioautographymentioning

confidence: 99%

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Galarce‐Bustos,

Obregón,

Vallejos‐Almirall

et al. 2023

Phytochemical Analysis

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“…21 In contrast, DB hyphenated to structure elucidation techniques, such as NMR, IR, and high-resolution (HR)MS, gives the impression of being instrumentally simple, time-saving, powerful in visual interpretation, applicable for diverse biological/biochemical/ chemical assays, and capable of high sample throughput and screening in parallel. [9][10][11][12]22 The planar chromatogram is directly subjected to biological/biochemical/chemical assays, and thus the correlation of chromatogram and bioautogram, which are two images taken of the same plate, is much easier if compared to HPLC-BCD or GC-BCD. Via HPTLC-UV/vis/ FLD-EDA-(HR)MS/NMR/IR, comprehensive chromatographic, spectroscopic/-metric, bioprofiling, and bioquantitative information of known and unknown bioactive compounds is obtainable in varying, complex sample matrixes, analyzed in parallel on the same plate in a single run.…”

mentioning

confidence: 99%

“…A latest study developed a streamlined structure elucidation workflow based on planar chromatography. 22 However, literature showing the potential of bioquantification of antimicrobial compounds using this bioanalytical approach is lacking.…”

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confidence: 99%

From Bioprofiling and Characterization to Bioquantification of Natural Antibiotics by Direct Bioautography Linked to High-Resolution Mass Spectrometry: Exemplarily Shown for Salvia miltiorrhiza Root

Jamshidi-Aidji

Morlock

2016

Anal. Chem.

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Phytochemicals are promising agents in the development of new antibiotics. A streamlined strategy for rapid screening and reliable characterization of antibiotics in botanicals was demonstrated in contrast to the commonly applied chromatographic column fractionation followed by microtiter plate assay. Modern direct bioautography hyphenated to structure elucidation techniques is a straightforward bioanalytical tool, especially if microbiological assays were taken into account. At one go, lipophilic antimicrobials in Salvia miltiorrhiza root samples were analyzed using high-performance thin-layer chromatography (HPTLC) in direct combination with Aliivibrio fischeri and Bacillus subtilis bioassays. The most intense antimicrobials were characterized via HPTLC-high-resolution mass spectrometry. As proof of this streamlined strategy, dihydrotanshinone, cryptotanshinone, and tanshinone IIA were identified and also compared with a reference. Two further antimicrobial zones in the bioautograms were tentatively assigned to be methylenetanshinquinone and tetrahydrotanshinone I (or its structural isomer methylenedihydrotanshinquinone). In another run, a validation study was performed for the bioquantification of ciprofloxacin and marbofloxacin via HPTLC-Bacillus subtilis. This pointed out the improved quality of the performance that was reached. Cryptotanshinone was biologically quantified in two S. miltiorrhiza root samples. Antimicrobials without an available reference standard were calculated as cryptotanshinone-bioequivalents. The results were of relevance, as 1 ng of cryptotanshinone was calculated to be bioequivalent to 0.6 ng and 2 ng of the synthetic antibiotics, ciprofloxacin and marbofloxacin, respectively. For the first time, quantitative direct bioautography via HPTLC-B. subtilis was shown as a reliable tool for streamlined bioprofiling of complex samples.

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Analysis of unauthorized Sudan dyes in food by high-performance thin-layer chromatography

2018

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Food authenticity and food safety are of high importance to organizations as well as to the food industry to ensure an accurate labeling of food products. Respective analytical methods should provide a fast screening and a reliable cost-efficient quantitation. HPTLC was pointed out as key analytical technique in this field. A new HPTLC method applying caffeine-impregnated silica gel plates was developed for eight most frequently found fat-soluble azo dyes unauthorizedly added to spices, spice mixtures, pastes, sauces, and palm oils. A simple post-chromatographic UV irradiation provided an effective sample cleanup, which took 4 min for up to 46 samples in parallel. The method was trimmed to enable 23 simultaneous separations within 20 min for quantitation or 46 separations within 5 min for screening. Linear (4-40 ng/band) or polynomial (10-200 ng/band) calibrations of the eight azo dyes revealed high correlation coefficients and low standard deviations. Limits of detection and quantification were determined to be 2-3 and 6-9 ng/zone, respectively. After an easy sample extraction, recoveries of 70-120% were obtained from chili, paprika, and curcuma powder as well as from chili sauce, curry paste, and palm oil spiked at low (mainly 25-50 mg/kg) and high levels (150-300 mg/kg). For unequivocal identification, the compound in a suspect zone was eluted via a column into the mass spectrometer. This resulted in the hyphenation HPTLC-vis-HPLC-DAD-ESI-MS. Graphical abstract Simplified clean-up by UV irradiation for Sudan dye analysis in food by HPTLC-vis-HPLC-DAD-ESI-MS.

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Streamlined structure elucidation of an unknown compound in a pigment formulation

Cited by 20 publications

References 36 publications

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

Application of effect‐directed analysis using TLC–bioautography for rapid isolation and identification of antidiabetic compounds from the leaves of Annona cherimola Mill.

From Bioprofiling and Characterization to Bioquantification of Natural Antibiotics by Direct Bioautography Linked to High-Resolution Mass Spectrometry: Exemplarily Shown for Salvia miltiorrhiza Root

Analysis of unauthorized Sudan dyes in food by high-performance thin-layer chromatography

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